I think a large part of the problem is that the younger generations have grown up with pretty strong expectations placed upon them to do things like go to college (at whatever cost), land a white collar job, climb the ladder, etc. The obvious solution is to own your decisions and start doing what you think is right for you, but it's far easier said than done to step out from under the expectations you've been saddled…
Certainly a six-figure salary is not necessary for happiness, but if you find yourself working long hours to make rent in some midwestern town it's going to cut into your opportunities for self-discovery and joy. And if you got wise a bit too late, after picking up federal student loans, you might well find that your dream career is genuinely off the table. (Found your true calling as a firefighter? Better keep up on those loans or you'll lose your license.)
It seems like we've created a system where the straight-and-narrow is increasingly narrow, and the cliffs around it are increasingly high. It's still worth finding one's own path, but in both social and purely-practical terms it's gotten steadily harder.